This WkndFreeSat, Jul 18, 2026·10:00 AMFREE EVENT - Vintage Car ShowChicago, IL · 1800 S Prairie Ave, Chicago, IL, United States, Illinois 60616Car Shows
This WkndSat, Jul 18, 2026·11:00 AM🚗🎶 Join us for the 1st Annual Friends of Hurley Car Show & Vendor Fair!Chicago, ILCar Shows
Jul25Sat, Jul 25, 2026·6:00 AMCar Show On The BoulevardChicago, IL · 6401 Stony Island Ave, ChicagoCar Shows
Jul25Sat, Jul 25, 2026·3:30 PMHobelman RegattaChicago, IL · Chicago Corinthian Yacht ClubBoats Marine
Jul26Sun, Jul 26, 2026·9:30 AMRainbow Regatta (Charity) Chicago, IL · Columbia Yacht ClubBoats Marine
FreeThu, Jul 30, 2026·5:00 PMThursday Cruise Nights Are Back! Harlem & Foster PlazaChicago, IL · Harlem & Foster PlazaCars Coffee
Aug1Sat, Aug 1, 2026 – Sun, Aug 2, 2026·2:00 PMColumbia CupChicago, IL · Columbia Yacht ClubBoats Marine
Aug7Fri, Aug 7, 2026 – Sun, Aug 9, 2026·2:30 PMVerve Cup OffshoreChicago, IL · Chicago Yacht ClubBoats Marine
Sun, Aug 9, 2026·3:00 AMOriginal Lowrider Car Show - ChicagoChicago, IL · 600 E Grand Ave, ChicagoCar Shows
FreeSun, Aug 9, 2026·9:00 AMVCOC Recurring Ride to Small Displacement SundayChicago, IL · Independence Park Advisory Council
Sun, Aug 16, 2026·9:00 AMSpinout Hot Rods And Customs 2026 Traditional Car ShowChicago, IL · Goyola ParkCar Shows$5
Sat, Aug 22, 2026·8:00 AM2nd Annual Car Show To Benefit USS Chicago Base Submarine Group WWII Submarine Memorial FundChicago, IL · Connie's PizzaCar Shows$20
Sat, Aug 22, 2026·9:00 AMSpectator Pass - Checkeditout 2026: The Chicago Porsche ConvergenceChicago, IL · 1350 W Fulton MarketCar Shows
Aug22Sat, Aug 22, 2026 – Sun, Aug 23, 2026·11:30 AMAlliance for the Great Lakes RegattaChicago, ILBoats Marine
